142769-27-5

Basic information

• Product Name: 5,6-DIMETHOXY-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 5,6-DIMETHOXY-1H-INDOLE-3-CARBALDEHYDE;5,6-Dimethoxyindole-3-carboxaldehyde
• CAS NO: 142769-27-5
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Mol File: 142769-27-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,6-DIMETHOXY-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIMETHOXY-1H-INDOLE-3-CARBALDEHYDE(142769-27-5)
• EPA Substance Registry System: 5,6-DIMETHOXY-1H-INDOLE-3-CARBALDEHYDE(142769-27-5)

Safety Data

• Hazardous Substances Data: 142769-27-5(Hazardous Substances Data)

Upstream product

• 14430-23-0 5,6-dimethoxyindole 
• 68-12-2 N,N-dimethyl-formamide 
• 88210-96-2 5,6-dimethoxyindole-2-carboxylic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 28059-24-7 methyl 5,6-dimethoxy-1H-indole-2-carboxylate 
• 157670-07-0 2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester 

Downstream Products

• 812652-87-2 5,6-dimethoxy-1-(4-methoxybenzenesulfonyl)-1H-indole-3-carbaldehyde 
• 812653-12-6 16-[5,6-dimethoxy-1-(4-methoxybenzenesulfonyl)-1H-indol-3-yl]hexadecan-1-ol 
• 812653-13-7 18-[5,6-dimethoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-octadecan-1-ol 
• 936829-13-9 benzyl-(5,6-dimethoxy-1H-indol-3-ylmethyl)-amine 

Relevant articles and documents

Methoxycamalexins and related compounds: Syntheses, antifungal activity and inhibition of brassinin oxidase

The phytoalexin camalexin is a competitive inhibitor of brassinin oxidase, an enzyme that detoxifies the phytoalexin brassinin and is produced by an economically important plant pathogen. For this reason, the camalexin scaffold has guided the design of inhibitors of brassinin detoxification. To further understand the structure–activity relationships of camalexin related compounds, the syntheses of monomethoxy and dimethoxycamalexins were undertaken. Four monomethoxy camalexins together with 4,6-dimethoxy and 5,7-dimethoxy camalexins were prepared from the corresponding methoxyindoles using the Ayer's method. The dimethoxy derivatives were prepared from the corresponding dimethoxyindole-3-thiocarboxamides using the Hantzsch reaction; however, this method did not work for the syntheses of 4,6-dimethoxy and 5,7-dimethoxycamalexins due to the lower reactivities of the corresponding indole-3-thiocarboxamides. The antifungal activity and brassinin oxidase inhibitory activity of all methoxycamalexins and ten camalexin related compounds were investigated. Among the 20 compounds evaluated, monomethoxycamalexins were stronger antifungals than the dimethoxy derivatives. However, remarkably, 5,6-dimethoxycamalexin, 6,7-dimethoxycamalexin and 5-methoxycamalexin displayed the strongest inhibitory activity against brassinin oxidase, while 4,5-dimethoxycamalexin displayed no inhibitory effect. Altogether the structure–activity relationships of camalexin related compounds suggest that the targets for fungal growth inhibition and brassinin oxidase inhibition are unrelated and emphasize that brassinin oxidase inhibitors do not need to be antifungal.

PPAR ACTIVE COMPOUNDS

Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.

Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres

In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared, 13c (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.

Propenone derivatives

The present invention relates to propenone derivatives represented by the following formula (I): STR1 wherein R1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, or YR5 (wherein Y represents S or O; and R5 represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituted or unsubstituted cyclic ether residue); R2 and R3 independently represent hydrogen, lower alkyl, or substituted or unsubstituted aralkyl, or alternatively R2 and R3 are combined to form substituted or unsubstituted methylene or ethylene; R4 represents hydrogen, hydroxy, lower alkyl, substituted or unsubstituted aralkyl, lower alkoxy, substituted or unsubstituted aralkyloxy, or halogen; and X represents substituted or unsubstituted indolyl; or pharmaceutically acceptable salts thereof.